


Just Date Me

by aerinth



Series: Just Do Me [2]
Category: Naruto
Genre: F/M, Fluff, Hatake Kakashi Is Trying, Mild Language, Nobody minds their damn business, POV Second Person, Prequel, Reader-Insert, alcohol use
Language: English
Status: In-Progress
Published: 2020-09-01
Updated: 2020-12-03
Packaged: 2021-03-07 02:48:19
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 18,065
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26219629
Author URL: https://archiveofourown.org/users/aerinth/pseuds/aerinth
Summary: You were single. Correction, you werehappilysingle. You absolutely, did not, by any means,needa relationship.However, the universe seemed to have other plans for you when you literally fell into Kakashi Hatake's life. Well, the universe and both of your meddling friends. If all turned out well, maybe you’d consider thanking them someday (but that really didn’t seem likely).[Kakashi Hatake x Reader] | Prequel to “Just Do Me”
Relationships: Hatake Kakashi/Reader
Series: Just Do Me [2]
Series URL: https://archiveofourown.org/series/1904212
Comments: 114
Kudos: 258





	1. Falling for You

**Notes for the Chapter:**

> Welcome everyone ＼（＾○＾）人（＾○＾）／
> 
> If you are new, know that this is the prequel to one of my other stories titled "Just Do Me" though it is not at all necessary that you read it. To everyone who followed along with "Just Do Me", thank you for coming to check this out and I hope you enjoy it just as much <3

You were single.

Correction, you were _happily_ single; had been your whole life. 

It wasn’t that you were opposed to dating, you just found a lot of comfort in your bachelorette lifestyle. As someone who enjoyed her freedoms and the pursuit of adventure, not being tied down to another person was preferable. In fact, for the past two years you had been traveling the Land of Fire in an attempt to bring better education to smaller villages. It had been an amazing opportunity granted to you by the Third Hokage, and you knew that wouldn't have been an option for you if you had been seriously committed to another person. Also, having the whole bed to yourself was kind of nice. 

Now that you were back in Konoha with an encyclopedia of new knowledge, you had a lot of work ahead of you. The curriculum restructure you had designed would take over a year to refine before it was ready to implement, but you were passionate about the project and prepared to work overtime to make it happen. The way you saw it, this was a big point in your career and you weren’t interested in letting messy, mushy feelings for a _man_ get in the way of your own success. No, you were happily single.

Unfortunately for you though, your friends didn’t seem to understand that. Which is how you ended up on a blind date at the most popular bar in the village. A date that (in your opinion) was not going particularly well. 

“If I had any other friends to replace you, I’d kill you for this,” you growled, sliding up to your violet-haired friend who was hanging over the bar top. “We’ve been here an hour and he’s already wasted, Anko!”

The woman laughed. “Hey, I told you he knew how to have a good time!” She gave you a firm smack on the shoulder before ordering both herself and you another drink. 

When the bartender pushed the cup of liquid your way, you frowned. “You do know that this isn’t really my idea of a good time anymore, right?” 

Anko brought her own cup to her lips and downed it in one gulp. “Ahh, no way! You’re never too old for a night out, (Y/n).”

You grimaced. “Anko, I have work-”

“I _know,_ you’ve got that fancy project and believe me, I am really happy for you! That is a big deal.” 

Her words were genuine, but you rolled your eyes because you knew there was more coming.

“ _But_ I don’t want to see you throwing away every weekend at the office either! Look, you just spent two years teaching kids in the friggin’ _sticks._ You’ve done enough good deeds for a lifetime, (Y/n). So try to let loose and have some fun again, will you?”

Giving you another gentle squeeze, she turned back to the group you had come with. You knew she had a point, but you were finding it hard to ‘let loose’ and ‘have fun’ now that you were left to return to your less-than-enjoyable date. With a heavy sigh, you threw back the drink Anko had bought and pushed away from the bar. You dragged your feet all the way to the high top table you and your date had secured in the corner of the establishment. 

“Did ya’ get ma drink?” the man slurred as you sat down. Your nose crinkled in disgust. 

“Hm? Oh, they were out,” you quickly fibbed. You had completely forgotten to grab him another beer. Offering to get the next round was honestly just an excuse to get away for a moment. You decided he didn’t need another drink anyways. If you were expected to spend the night with him, it was in your best interest to cut him off now. 

Your date disagreed.

“What?!” he shouted in protest. “That’s ridic-ulous. It’s not even eleven!”

 _“Tell me about it,”_ you murmured, not at all in reference to the bar being “out” of alcohol. 

A determined look stretched across your date's face as he attempted to stand. Planting two firm hands on the tabletop, he slipped from his stool (almost eating shit as he did) and turned for the bar. “I think I’ll give them a piece of my mind about their _poor service,”_ he spat, drool dangling from his mouth.

“Wait, please don’t-” 

He was already halfway across the room (he was quite speedy for a drunk man). You heard his palms smack on the bar top alerting everyone working and anyone else within a few yards that he was an unhappy customer, and took it as your cue to leave. Can’t say you didn’t try; he was someone else’s problem now. 

You slipped from the crowded hall before anyone could notice you were leaving. The night air was cool, and felt refreshing on your heated cheeks. You wouldn’t go far. Anko was more than capable of taking care of herself, you knew, but you’d never hear the end of it if she found out you bailed early. Instead, you found sanctuary in an empty alley around the corner of the bar. The quiet soothed your ears and the night stars that were visible thanks to a clear sky softened your gaze.

Going out like this always made you feel stressed. At least, it did ever since you got back from your travels. You used to be able to throw back shots no problem. You’d stay out all night, sleep in late, and do it all over again the next day. It was fun, until it wasn’t. 

Something changed when you were away. You had gained an appreciation for culture and life outside of partying. You wanted to focus on your job and your personal growth. If you ever _were_ going to date a man, it would have to be someone who took you seriously; not like this loser Anko had set you up with. To him, you were just a good time. No, you wanted to be with someone who could keep up with your goals. Someone who didn’t expect you to wait around for them all the time. Someone who wanted to enjoy life _with_ you. 

Leaning back against the wooden walls, you smiled to yourself. If you were being honest, all of that sounded really nice. But you weren’t going to get your hopes up. If the date Anko rustled up for you signified anything, then finding that type of guy around here was going to be near impossible. 

You shook your head and let out a deep breath of inhaled fresh air. These were silly thoughts. 

“You don’t need anyone, (Y/n),” you said to yourself. “Remember that.”

Standing in the alley alone, you obviously weren’t expecting any sort of response to your words, so when a desperate mewl came down from just above you, you startled. You looked up to the roofline and saw a small, gray kitten perched on the edge of the building. His large yellow eyes were filled to the brim with fear, and his whole body was visibly trembling in the light of the moon.

“Uh oh, are you stuck little guy?” You surveyed your surroundings when he meowed again, softer and meeker this time. “Hang on. I’ll get you down.”

It would have been easy enough to jump onto the roof and snatch him (you were a shinobi after all, even if you were a little out of practice), but you knew the risk of spooking him was too great. If he was startled, he might fall from the roof and you weren’t sure he was old enough to stick the landing. Maybe if you climbed up there, he would come to you instead. Still, the only thing climbable nearby was a wooden fence that was about ten feet high and split the alley in half. It would get you close enough to the kitten, but it was only about two inches thick. You’d have to be really careful.

With several hops and one swing of your leg, you hoisted your body up onto the fence and balanced yourself on the thin wood. The kitten seemed more than grateful for your assistance, and he ran to you as you approached the roof. With one hand stabling itself on the shingles, the other was free to scoop the stranded animal into your arm. He licked your cheek in delighted gratitude.

“Okay. Hold on little dude, I’m going to get you down-”

Your words were sincere, but spoken too soon. The first shift in your weight sent your foot sliding from the fence. Your free arm flailed, searching for anything to grab onto to prevent the fall, but had no luck. You slipped from the fence line with an expletive, and you and the gray kitten headed for a hard landing on the dirt. 

///

Kakashi Hatake did not want to be out tonight. He had just returned from a very long mission, that was barely a success, and he _wanted_ to be in bed. However, when his fellow jonin invited him out for the evening, he realized he was fresh out of good excuses. Having already used his best lines this week, he had no choice but to accept the offer begrudgingly. 

He only planned to make a quick appearance; showing up for even half an hour was typically enough to get them off of his case for a few more outings. Still, the thought of even that much time in a crowded bar had him feeling queasy, and he was looking (begging, really) for any possible reason to be late when his eyes fell on _you._

He stopped walking, kicking up some dirt because of the suddenness. With a blank stare, he watched as you hopped in place several times before swinging a leg up and clambering the fence in the alleyway. His brow furrowed into a look of concern. 

_What an odd woman,_ he thought, watching you wobble. _I guess Naruto was right; the village weirdos_ are _getting weirder._

After another moment, Kakashi decided that whatever it was you were doing was certainly none of his business. He gave a shrug of his shoulders and turned away, heading for the bar. Not a second later, he was stopped again by the sound of a soft mewl. His gaze wandered back to you and then over to the roof where he saw the tiny gray kitten, and the pieces began to click together in his head. His face fell flat.

_Well now, this is going to end poorly._

That type of thinking didn’t seem to be slowing you down though, and Kakashi continued to watch as you inched towards the rooftop. You had stretched out an arm, now only having one to balance, and clicked your tongue at the cat as you moved in closer. With every step, your bodyweight shifted, and Kakashi became more amused by your fierce determination. He knew the wood must have been slick because it had rained just the other night, and honestly it would be a miracle if you made it back down safely. Sure enough, your sandal slipped from the fence not a second after you had secured the kitten. 

_Yup, called it._

With a bored sigh, he gave a quick look up and down the street only to determine that, yes, he was in fact the only adult within a hundred feet and thus the only one who could help. Honestly, when he had asked for a distraction he was hoping for one that involved a little less... work, but he supposed beggars couldn't be choosers. He wanted a reason to be late, and the universe had given him you. That would do fine enough. Kakashi moved to sprint towards you, not at all knowing that after he touched you for the first time, he'd never want to let go again.

///

The kitten cried in your arms as you both fell towards the ground. Your only goal was to keep it safe in your hold so it wouldn’t end up underneath you by some terrible mistake. 

Much to your surprise however, you never hit the dirt. You were still quite jostled by the sudden feeling of two strong arms wrapped around you, each holding you with confidence and skill, but it hardly compared to getting the wind knocked out of your lungs. 

As soon as you figured out what had happened, you were already being set back on your own two feet. The kitten appeared calm and unfazed now that you weren’t a victim of gravity, but your own heart was beating double time. After taking a few deep breaths, you looked up to see the face of your savior only to have your heart leap from the starting gates again, and your soul almost leave your body. He was _stunningly_ handsome. Even with two-thirds of his face covered, you knew he was a looker. The mask covering his cheeks didn’t hide the strong jawline, and the village headband didn’t keep you from noticing the captivating, alluring, darkness shining in his visible eye. His hair shone like starlight, and looked as soft as sheep's wool, and there was a lingering feeling of loss on your skin ever since his fingers parted from your body.

Kakashi gave no indication of this, but while you were practically drooling over his features, his mind was running away with similarly sinful thoughts. After setting you back down safely, he had come to the realization that this woman he had initially labeled as a village crazy-lady was actually a captivatingly beautiful kunoichi, not much younger than him. He found himself lost in the (e/c)s of your eyes, that were shining like precious stones. The (h/c) strands that framed your face fell perfectly, and didn’t look at all like you had just taken a nasty tumble. Kakashi had encountered plenty of attractive women before, but something about you made him want to stare forever. 

The desire to keep looking at you was uncomfortably overwhelming and he had to shake away his thoughts before speaking again.

“Are you alright?” he asked, and you were instantly pulled back to the present. 

“Oh, y-yes,” you stuttered out. “Thanks.”

When you locked eyes again, you both seemed to fall into an intoxicating trance; one you could have stayed in all night if Kakashi hadn’t torn his gaze away, clearing his throat. 

“You know, that cat got himself up there. He probably could have found his way back down.” He gestured to the animal still happily hanging in your arms.

You let out a small giggle that made Kakashi’s heart skip, and if it weren’t for his mask he was certain his cheeks would have betrayed his efforts to appear emotionally un-compromised with a blush. 

You placed the cat on the ground and gave it a soft pat on the head before saying, “I guess you’re right. He asked me for help though, so I had to try.”

Kakashi hated that he couldn’t pinpoint what was different about you. It had to be something, because he had never found it so hard to focus. There was a small voice in his head that told him to leave, to say goodnight now and hope he never saw you again so he wouldn’t have to be plagued with this new, distracting curiosity. 

But a louder voice said stay.

“What were you doing out here alone?” 

The concern in his question seemed to catch you off guard and you waved a hand dismissively with a soft smile. “Oh! I was probably going to head back in soon, actually. A friend set me up on this silly...”

As your voice trailed off, so did the warmth in it. Your gaze moved behind Kakashi when you saw a man stumble out of the bar's entrance. You recognized him immediately as your drunken date, as if you had summoned him with your words. He toppled over the railing, his head nearly hitting the ground before the entire contents of his stomach was expelled onto the pathway.

You tried to mask the disgust on your face with a smile but something inside of you twisted and you realized that the absolute last place you wanted to be in this very moment was back inside of that bar on your date, and your next words tumbled out of your mouth before you could even register them in your brain. 

“Go out with me!” you all but shouted at your rescuer, causing him to take a step back in fear. With a deep blush of embarrassment coloring your cheeks, you recovered softly, “I mean, let me buy you a drink. As a thank you.”

He didn’t respond for a moment. Kakashi hadn’t missed the way your eyes drifted behind him to something that had triggered such a sudden shift in demeanor, but he hardly had a chance to analyze that, as his own thoughts were pulling him in every direction. That small voice that told him this - _you_ \- would be trouble, continued to mutter in the back of his mind. You had just shouted at him like a lovestruck teenager, even though you were nothing more than a stranger. (Maybe you were a village crazy lady?) Not to mention that if he went with you, his friends would certainly notice, and the string of questions to come would be brutal. 

But the louder voice, the voice Kakashi _wanted_ to listen to, told him to go. Get to know you. After all, it wasn’t like you had asked to date him. It was just one drink.

Finally, he conceded. “Okay," Kakashi hummed. "After you.” He stepped to the side, making a clear path to the bar you had just come out of. 

Rather than lead on, you turned and pointed in the opposite direction. “Actually, I was thinking about trying out that new place, just up the road? I hear it’s a little less...noisy.”

Kakashi paused. It was amazing really. You were, anyways. He had never liked the feeling of someone getting inside his head, but in this moment he was relieved that you had practically read his mind. 

“Say no more.” He moved to begin walking, but was stopped by your outstretched hand.

“I’m (Y/n), by the way,” you said, your voice soft and sweet. 

He eyed your fingertips carefully, and then a cheeky smile stretched out under his mask as he said, “Kakashi Hatake,” with a nod. 

Rather than shaking your hand like you had expected, Kakashi suddenly grasped your fingers softly in his own, and swiftly looped your arm under his. It may have been an impromptu outing, but Kakashi knew how to be a gentleman when he wanted to be. 

“Alright then, (Y/n). Shall we?” he asked. 

You only hoped he didn’t notice the deep blush that painted your cheeks when you nodded.

As you headed down the road together, your mind began to spin with questions of whether or not this was a good idea. You, who was comfortable and happy as a single woman, who was serious about her job and her personal growth, had just asked a man out for a drink. It felt sacrilegious. You also knew Anko would lay into you with questions tomorrow, and you weren’t looking forward to that either. 

Taking a breath, you had to shake the thoughts from your brain. You were getting way too far ahead of yourself; there was no need to spiral. After all, it wasn’t like you had asked to _date_ him. 

It was just _one_ drink.

**Notes for the Chapter:**

> Lol I rewrote this chapter three times because I was honestly in a panic over making this meet-cute good enough. 
> 
> Gods help me going forward because beginnings of relationships are not my strength, (but tomfoolery is and ya'll better believe there will be tomfoolery!)
> 
> In other news, I will obviously continue to work on my unfinished projects here on A03, but a few times while writing this chapter I became very insecure that my writing was bad? Like, I lost my mojo or something, I don't know. 
> 
> Anyways, hope to see you next chapter! Here is my [tumblr!](https://aerinth.tumblr.com/)


	2. Hard to Get

“Wait, wait, _wait_ , let me just get this straight-”

You let out a deep sigh that could hardly be heard over the laughter coming from your long-time friend and colleague who sat across from you at your kitchen table. 

“You, _you,_ (L/n), (F/n), miss _‘I want to be single and focus on my career’_ went outside last night to escape your date, only to ask _another man_ on a date? And then you stayed up all night talking with him at a different bar? Is _that_ what you’re saying?”

You rolled your eyes as you responded. “No. I already told you, Anko, it wasn’t a date-”

She didn’t even let you finish before she busted out in a fit of laughter again. “Oh man, this is _amazing!_ I can’t wait to tell everyone!”

“Don’t do that, please,” you said between grit teeth. Why’d you have to be so unlucky as to have a best friend that was such a gossip? “It wasn’t anything serious okay? I was just paying him back for saving my dumb ass.”

Anko eyed you with a cat-like grin. “(Y/n), come on, be real. Maybe that’s what the first drink was, but what about the one after that? And the one after _that?_ That’s not paying someone back, that’s an excuse to keep talking.”

Your cheeks instantly filled with heat. There was maybe some truth to what she was saying; you had unexpectedly enjoyed yourself. Talking with Kakashi turned out to be very easy, and you didn’t think it was just because of the alcohol. There was something about him that you felt connected to. 

And you wanted to feel more of it. 

But you certainly weren’t going to admit that to Anko so she could tell everyone. So instead you crossed your arms and huffed. 

“You’re being ridiculous,” you snorted. 

Your attitude didn’t faze Anko even a little. “Do you want to see him again?” she asked, with a cheeky tone. 

Your eyes snapped to hers in a glare. _“What?”_

It wasn’t so much that you didn’t know your answer, you just didn’t want to say it out loud. 

All the same, she repeated herself with a grumble. “Do you _want_ to see him again? Really, (Y/n) it’s not that hard to answer.”

You threw a firm pout in her direction, but you knew she was only going to keep pressing and pressing until she got some sort of response out of you; it really was in your best interest to give her something. 

Turning your attention back to your tea, you answered in a tone that suggested indifference. “I guess it would be fine if I did.”

Unfortunately for you, that was just enough for Anko to run with. _“Alright!”_ she cheered, throwing a fist in the air. “Then you listen to me, okay? I’m going to give you the best advice. He’ll be clawing at your bedroom window every night!”

She was too busy whooping and hollering to notice the look of sheer uncertainty that graced your face. You didn’t really think you wanted Kakashi to be ‘clawing at your window’. And even though you had only spent a few hours with him, you were fairly sure that wasn’t something he would do, and so you weren’t really sure you needed Anko’s advice at all. 

But, she was too far gone now. You had to at least hear her out. 

“So, I’m glad you had a great time and all, but first thing you need to learn is that you can’t go letting a man have that much attention so fast. If you want him to know that you’re serious, you have to play hard to get.”

She flashed you a toothy, confident grin but you only blinked in response. Sure all of this stuff was new to you, but now it was like she was speaking a whole other language. 

Stumbling over your words a little you asked, “I have to play… what?”

Anko’s face immediately fell into a frown. “Ugh, (Y/n)!” she groaned. “I mean you have to make it a challenge for him. If you’re one of those girls that just throws yourself at him, he won’t be as interested!”

You stared back at her dumbstruck. What she was saying didn’t make any sense. You had already gone out with him once, what was wrong with just doing it again? You also couldn’t deny that feeling of instant attraction you had experienced. You couldn’t say for certain that Kakashi had felt it too, but he certainly seemed interested in you. If both of you already enjoyed spending time together, you saw no reason that you couldn’t just keep doing that. 

“I don’t know, Anko,” you said awkwardly, a little nervous to be voicing your concerns to your abrasive and stubborn friend. “We had a really good night together, maybe I should just be myself with him?”

Sure enough, Anko wasted no time in sharing her disagreements. _“HAH!_ My little spring chicken, you are too cute!” She gave you a tender pat on the head and you grimaced.

“You aren’t making any sense today,” you spat.

Anko only laughed before taking another gulp of tea and continuing. “Look, take it from a woman with experience. If it went as well as you say it did, then next time you see him he’ll ask you out again.”

Something in your chest fluttered at her statement. Something you could only identify as excitement that someone else agreed that Kakashi was maybe interested in you. It made you feel a little less silly for maybe being interested too, and willing to hear Anko’s suggestions. 

Almost in a whisper you said, “Are you sure?”

Anko smiled. “Yup,” she stated confidently. And then her bright demeanor switched to one of complete seriousness. “And then you’ve got to tell him _no.”_

Now she had really lost you.

“What?!” you barked, utterly confused. “But I don’t want to tell him no! You _just_ asked me-”

She cut you off again with a palm smacking the top of your wooden table. “It doesn’t matter, you just gotta!” she commanded. “You have to make him chase you, get it? Trust me, okay? I promise you’ll thank me later.”

There was a feeling in your gut that wasn’t so sure about that, but still you didn’t argue. After all, Anko did have a lot more experience with men. Maybe it was possible that she knew something you didn’t. 

///

The rest of your morning continued on as normal. You arrived early to your office, which gave you just enough time to prepare for the day and get a head start on some budgeting you had to do for your side project. A project you had to continuously remind yourself you were invested in and serious about, because your thoughts kept drifting off to your evening out, and to Kakashi, and the way his shoulders shook when he chuckled, and the way his dark eyes seemed to be only on you. Even though you knew he was watching everything around him constantly, you felt like the only person in his world at that table with him. 

You had meant what you said. It would be fine to see him again. Honestly, it would be quite… nice.

“Good morning.”

The cheerful greeting came from your doorway, and you almost tossed your book from your hands as it startled you. 

When your eyes fell on your visitor, your chest tightened and your breath suddenly seemed to escape you.

“Kakashi,” you acknowledged in almost a whisper, before clearing the desire from your voice. “Hi. I mean, hello, good morning. What brings you here?”

Kakashi kept a straight face when he spoke, but inside his heart was doing weird things that he didn’t understand outside of a mission. It was skipping and stopping and racing and it had been all morning when he thought about you, and he was damn near tired of it. He wasn’t stupid, he knew there was something he liked about you, or liked about being around you. He had felt it the instant his fingers landed on you yesterday. What it was though, he couldn’t put his fingers on that. And when he still couldn’t figure it out after getting pretty crappy sleep over it, he decided to just visit the problem at its core. You.

Of course he wasn’t going to tell all of that to you though.

“Oh, well I was actually just running some errands this morning, minding my own business, when a wild dog appeared and chased me all around the block until I ended up here. So, I figured I might as well come say hello,” -he flashed you a bright eyed smile- “since you _did_ tell me to drop by sometime.”

Heat suddenly pooled in your cheeks and your forehead as you remembered telling him where to find you after he walked you home last night. “I did!” you squeaked, and Kakashi laughed. His shoulders shook and then relaxed, the way they had when he laughed with you last night and you loved it.

“So I was thinking,” he began, stepping further into your office and coming to stand in front of the desk you were working at. “Since we had a pretty good time last night, maybe you’d like to go out again? It doesn’t have to be anything spectacular, but if you wanted to go for another drink-”

Your (e/c) eyes shot up to Kakashi, wide and sparkling. “Are you serious?” 

He said it so casually. It was intentional on Kakashi’s part; he couldn’t have you knowing yet just how much he liked being around you. Not when he couldn’t even figure out why or what to do about it himself. To you though, all you heard was Anko. Like the devil on your shoulder she kept cheering “I told you so!” because she had. If she hadn’t, you never would have thought anything more of Kakashi’s proposal because as far as you were concerned, men like Kakashi didn’t really exist without a catch, and if they did, they certainly wouldn’t be asking out little ol’ you. 

Kakashi stared at you, a little confused. He wasn’t sure he had said anything that should imply that he was joking. “Um, yes?” he said awkwardly but reassuringly. 

You replied under your breath, not intending for him to hear you. “Wow that sounds really nice,” you said, because it did. You _wanted_ to go out with him again. You _wanted_ to sit and talk with him again. 

Kakashi smiled confidently hearing your words. “Okay then. Should we plan for tomorrow?”

The little Anko devil on your shoulder was suddenly shouting again, and shouting loudly. She reminded you that 'if you wanted him to really like you,' you were supposed to be playing hard to get. That still made no sense to you, but this was all new territory, and you really did want him to like you...

 _“No!”_ you practically shouted because you had to fight off the ‘Yes’ that was trying to squeeze it’s way out of your mouth instead. 

Kakashi stared at you, dazed. “Uh… no?” he clarified. That was a turn he was definitely not expecting the conversation to take. 

Neither were you honestly, but you had made your bed and now you were going to sleep in it. 

“Yes, no,” you said firmly. “I can’t. I already have plans.”

That didn’t do anything to help cure Kakashi’s confusion, but he attempted to move on casually all the same. “Okay then how about the next day?”

Your stomach dropped. Damn, you hadn’t anticipated him to be so insistent. Anko didn’t give you any warning about that. When she said ‘say no’, you didn’t think she meant you’d have to keep saying no. All the same, this was what was happening and you had to stick with it.

“Actually,” you said, standing from your desk. “Unfortunately, I just remembered that I am previously booked until further notice. Apparently.”

Inside you were cringing and squirming in discomfort. It was so awkward, and you knew it. You knew it even before you saw the look of sheer alarm and confusion on Kakashi’s face. Not meaning to throw more salt in the wound of his rejection, you headed for the door and with a firm bow said, “Goodbye.”

You turned and marched stiffly into the hallway, leaving Kakashi standing puzzled and alone in your own classroom. 

///

“You’re quieter than usual.”

Kakashi straightened and pulled his distant gaze back to the present and to his friend that sat across from him at the tea shop.

“Hm? Oh, yeah. Sorry.” Kakashi knew he had been spacing out, but he hadn’t expected Asuma to notice. He figured he must look really confused if other people were seeing it too, but he wasn’t sure how to help it. All day, his mind had been clouded with you and how quickly you had shut him out. For the first time in a long time, Kakashi felt stuck.

“What do you know about (L/n) (F/n)?” He figured there wasn’t much harm in asking around just a little, if he wasn’t coming up with any answers on his own.

Asuma blinked. “You seriously asking about a girl?”

He gave a look like the world was ending and Kakashi shifted uncomfortably beneath it.

“Well, I-” Kakashi sputtered, searching for any type of cover to explain what had brought on his sudden attentiveness to the opposit sex. “I have reasons to believe she’s worth investigating,” he said matter-of-factly.

Asuma gave him a doubtful glance. “Right…” he drawled. He clearly wasn’t buying it, but he gave in all the same. “Not much, I guess. She comes out with the usual crowd occasionally. She’s pretty close with Anko it seems, but other than that I haven’t heard much. What’s got you interested?”

Kakashi stiffened. “She-” he started, but instantly became cautious of how much he wanted to share. He had always liked to keep his business private, but one way or another he needed some assistance here. So he went with the truth. “Last night, we got a few drinks together. It wasn’t anything really, but, you know,” -he cleared his throat awkwardly, not used to talking about himself like gossip- “ _I_ thought it was a nice time. Anyways, I saw her again today and, of course being the gentleman that I am, I asked her to go out again and she said _no._ ”

There was a moment of silence, and Kakashi’s disclosure hung over him like a weighted blanket. Then, Asuma let out a deep, hearty, amused laugh. 

“Well, well. Kakashi Hatake has finally met his match, and it’s a _woman._ Who woulda thought?”

Kakshi raised a brow. “I don’t know about that,” he asserted. “But something was definitely off. I know I only just met her, but last night I felt this sort of.... connection. A spark almost.” He sighed, feeling the sting of his defeat. “I can’t explain it. Either way, today it felt like it was gone. She seemed completely disinterested, and it doesn’t make any sense.”

Asuma, trying to be polite, had to keep from chuckling at the pout that was forming on Kakashi’s face. It was amusing that for once he seemed to know something Kakashi didn’t.

“She’s playing games with you, Kakashi,” he stated.

Kakshi didn't have the slightest clue what he meant. “She _what?”_ he asked.

Asuma took a drink from his tea before saying casually, “You know, like pretending to not be interested in you when she really is? Girls do that stuff all the time.”

Kakashi paled in shock. _“Do they really?”_

Asuma's mind was already running away with thoughts about what Kakashi had just told him. “Tch, I bet Anko is planting every idea in her pretty little head,” he grumbled, but still seemed slightly amused. “If that’s the case, I don’t envy you; you’ve got a tough challenge ahead.”

Asuma was familiar with how Anko worked. He hadn’t heard enough about you to know what your motivation in all of this was, but he had a pretty good feeling that he was right about Anko pulling the strings here. 

Kakashi on the other hand was deeply confused by this news. It made no sense to him whatsoever that you would feel the need to act like you weren’t interested if you actually were, or whatever Asuma had said. But Kakashi was a man of strategy and he knew that it was useless to ask how the situation could have been set up differently. He needed to ask himself what to do with the situation he was already in. Unfortunately, he had no idea.

“What do I do then?” he asked Asuma a little sheepishly, but really he was desperate for the answer.

Asuma snorted and gave him a wicked sort of grin. “Well it’s obvious isn’t it?” He set his cup down on the table and his eyes sparkled with a competitive fire. 

“You have to beat them at their own game.”

**Notes for the Chapter:**

> Another one down! I am seriously having so much fun writing their story, I can't~ Thank you to everyone who showed love. I'm completely blown away by how many people are invested already, and it makes me so happy that people want to read what I write. 
> 
> Hope to see you all next time, but again feel free to connect with me on [tumblr](https://aerinth.tumblr.com/) until then!


	3. Playing the Game

You felt awful. Having to actually work the whole day just made things worse. You hadn’t wanted to turn Kakashi down, and on top of that you did it so awkwardly. Who runs away like that?! You were genuinely so mortified that even your students had noticed you were off. The salt on the wound was that eight-year-olds have no problem calling people out when they look troubled. 

_“Y/n Sensei, your hair’s messy!”_ Yes, because you had been tugging on it all day. 

_“Y/n Sensei, your nose is doing that weird twitchy thing again!”_ Yes, because you were stressed. _Very much so._

However Anko planned on making this work, you weren’t sure. From your perspective, it would take a miracle to dig your way out of the muddy grave you had buried yourself in just a few hours ago. So, you wasted no time in tracking down your nosy, scheming friend at the end of your work day just so you could ask what exactly she intended to do now that you had turned down the only man you had ever maybe actually liked. 

Her face brightened the minute she opened the door to her apartment and saw you standing in it. She knew what you were there for. “Ooh, he came by today, didn’t he?”

You pushed past her, kicking your shoes off at the door. “Yes and-“

“Did he ask you out?”

You sucked in a breath. “Yes, _and-_ "

“Oh HO, I knew it!” She bounced around you cheering. “What did he suggest? Drinks tomorrow?”

With an exhale, you shut your eyes; her enthusiasm was making you nauseous. “Yes, AND-“

“Oh my god, I am so good! Did you do what I told you to? Did you turn him down?” Her eyes were wide, and sparkling, and _prying._

 _“YES!”_ you erupted, your pent up emotions from the whole day finally tumbling out of you. “And I _hated_ it. Anko, it was so embarrassing, and I could tell he was really confused.” You flopped onto a chair with a pitiful pout. “How was this supposed to help exactly?”

Anko laughed, taking a seat beside you. “Oh, it doesn’t. Not at all. It’s the next part that’s really important.”

You stared back into her hazel eyes, a little tired, a little disgusted. When she told you the plan was to play hard to get this morning, you had assumed that would be it. You kicked yourself for not asking if there was going to be more. There was always something more with her.

“Which is…?” you urged, realizing she wasn’t going to tell you on her own. 

A wicked, cat-like grin stretched out in front of Anko’s teeth and you gulped. 

_“You’re going to go anyways,”_ she practically hissed.

Your face fell. “Excuse me?”

She had to be joking. This time, she just had to be. There was no way that she was telling you to go on the very date you had just turned down, because that would be preposterous and crazy.

Of course though, she was dead serious. “He asked you to go out tomorrow, right? So, you go out tomorrow. Wherever you think he was going to take you, that’s where you go and he’ll be there.”

You frowned and crossed your arms with a huff. “How could you possibly know that?”

“Because I know!” Anko asserted. She gave you a reassuring pat on the back when you only responded with a raised brow. “Trust me, when a guy gets rejected, he tells his friends. Then you know what they do? They take him out drinking. And when you show up out of nowhere, that’ll be what drives him crazy.”

“And this is a good thing?” you hummed, not thinking ‘driving someone crazy’ really sounded like the relationship you wanted. 

But Anko assured you it was, and her confidence overpowered your doubt and any objections you might have had. “You bet,” she smiled. “Now, go get showered; you smell like children. And,” -she flashed a cheeky grin- “Make sure to wear your best outfit.”

///

Kakashi was not an expert on dating, or on women, and he knew this. But he had read enough romance novels to understand that when a woman said ‘no’, she typically meant it (even if her pursuer disagreed). So, even though your rejection of a second date and your sudden emotional unavailability _baffled_ him, he felt a little uncomfortable continuing to seek out your affections as Asuma had instructed. Even if he didn’t feel the same way -meaning he _did_ want to go out with you again, very much- he knew what ‘no’ meant, and he wanted to respect your decision and move on. 

However according to Asuma, that was not at all the right thing to do, and he had convinced Kakashi to go along with his plan for at least one night. 

“Just one night,” Asuma had said. “If I’m wrong, we’ll forget about it. If I’m right… well, you can tell me where you want to go from there.”

And that was how Kakashi ended up out at a bar for a second night this week, only this time Kakashi was not as enamored with his company. 

“Quit looking so nervous. You’re going to scare her off.”

Kakashi shifted in his seat, attempting to look more relaxed. This wasn’t the first criticism he had received from Asuma tonight, and he clearly wasn’t doing a very good job of applying the feedback. “Sorry,” he replied to his friend flatly. “I’m just so unsure about this.”

Asuma took a drag of his cigarette and then blew the smoke out into the cool air of the outdoor bar. “What’s the worst that could happen?” he shrugged.

Kakashi’s brows raised. “You don’t _really_ want me to answer that do you?”

Kakashi could come up with at least five things that could tie for ‘the worst thing’ that could happen tonight. Again, he wasn’t an expert, but he didn’t have to be a love guru to know that playing games with people’s feelings (even if it involved his own) was a dangerous endeavor. And Asuma, confident that Anko was playing for your side of the board, had a very presumptuous plan set into motion for this evening. Kakashi was just the moving piece at this point and he didn’t like it one bit. 

He sighed and dropped his head onto the bar counter. Kakashi was good at a lot of things, but this? He let out a sigh. “I’m not sure I’m cut out for this type of pressure.”

With a small laugh, Asuma elbowed him in the side. “Don’t chicken out now; they just walked in.”

Kakashi was sitting upright in an instant, his head turned and gaze locked on the entrance of the bar. Sure enough, there you were. He maybe would have been more amazed that Asuma was right in suspecting you’d show up, if he wasn’t so distracted by how _stunning_ you looked. Immediately he felt a wave of pleasure wash over him: the same kind he had felt when he looked into your eyes for the first time just a night before. He had thought you looked nice even after you fell from a roof, so he was especially captivated by the way you had dressed yourself up so sweetly this evening. You looked beautiful, _radiant_ ; your head was held high and you were smiling at something Anko had whispered in your ear. The desire to feel every curve of your body and touch every inch of your skin sent a shiver up his spine; he could practically imagine it, and it drove his senses wild. It would have been impossible to look away if not for Asuma speaking up and grounding him back in a reality where you were so close and yet so far from him. 

“Heh, and you doubted me. I should’ve made you put money down.” Asuma chuckled, turning back to the bar. When his gaze shifted to something on his right, he let out a small hum. “Oh, and just in time too.”

Kakashi swiveled to follow Asuma’s eyes, just as another person approached them.

“Hey Kakashi. It’s been a long time.”

///

As you walked into the courtyard of the outdoor bar, you thought it felt nice to be confident in the outfit you had picked because you were not confident in Anko’s plan of crashing the boy’s night of a man you had just rejected. It felt silly and extraneous. You still weren’t even confident he was going to be there, like she had said.

Until your (e/c) eyes found a mop of starlight hair seated at the bar, and your stomach sank.

“Anko, he’s here…”

“Huh? Where?” Your friend spun around, her own eyes frantically searching for her target. When she found it, she didn’t notice the same thing you had. “Wait, _Kakashi?_ ” she sputtered. “The mystery man that stole your heart is _Kakashi Hatake?_ Why didn’t you tell me?!”

Your nose scrunched. You weren’t sure your heart had exactly been stolen. He was _just_ a guy. Like, any other guy, right? 

“Uh, should I have?” you asked. You didn’t know why it mattered. Also, if she had wanted to know his name, she could have asked. 

But clearly it did matter, because Anko erupted in delight. “This is crazy. This changes everything. Hah, I should have known that some average loser wouldn’t have been good enough for your tastes (Y/n). Alright new plan-"

“Wait Anko, stop.” You raised a soft hand, silencing her before she could get carried away. Your misty eyes were still looking in Kakashi’s direction. “I don’t think it matters anymore.”

She turned, eyes curious. “Why not?”

Your words came out slow and soft. “He’s with another woman.”

You didn’t need to point with your fingers. Your gaze was trained on her, practically drilling holes. Anko followed the line from your narrow pupils to the bar. She watched Kakashi and the newcomer for just a moment. You could practically hear the gears turning in her head. While you were ready to sink into your defeat and move on, Anko was making a plan, because something didn’t line up. Just as you were about to tug on her sleeve and ask if you could leave, she startled with a realization.

“Hold on, I know her.” 

You were about to ask for clarification, and question why Anko suddenly looked so amused -possibly even a little pleased- when she spoke up again. 

“Looks like you’re not the only one playing hard to get (Y/n).”

///

“I don’t think I’ve seen you since we were kids.”

Kakashi feigned interest with a forced smile. “Oh, has it been that long?”

This had been Asuma’s big plan. The one that had made Kakashi think of at least five things that could be ‘the worst thing to happen tonight’: another woman. An old acquaintance who was back in town, actually. It was a little tasteless in Kakashi’s opinion. He didn’t think making you jealous was the right way to kickstart a budding romance, but Asuma had assured him that since you were the first one to initiate a challenge with your rejection, he was obligated to respond. Also apparently being seen with another woman was supposed to make him appear more desirable which would somehow grab your attention. Or something. Again, Kakashi did not understand any of this, but he also couldn’t exactly tell the nice girl to get lost now, could he? (Actually, _could he?_ No, better not.)

“Well, tell me everything! How’s life been treating you?” She was at least genuine, and she was trying.

Still, Kakashi didn’t exactly know how to summarize everything that had happened in his life since the academy days. Would ‘experiential’ be underplaying it?

“Uh, well-” he started but was thankful he didn’t have to finish. 

In a very quick instant, Anko had appeared and tethered herself to the girl in an aggressive bear-hug. Kakashi, alarmed at first, quickly realized what was happening when he saw you standing only a few feet behind her. He was sure Asuma, who was probably sitting in some corner of the bar observing, was patting himself on the back for being right. 

“Wow, hey _you!_ ” Anko said boisterously to cover-up the fact that she didn’t remember this girl's name in the slightest. “It has been forever, how have you been!?”

The girl frowned, trying to regain her balance with little luck. “Oh Anko, hi.” Her tone was far from amused. “I’m fine, but I’m actually out with-“

Anko cut her off with a forced laugh. “That is _great,_ you’ll have to tell me all about that over a drink. On me.” 

The girl made a disgruntled face, but tried to respond politely. “Oh well, no worries. I actually already have one.”

She shook her bottle to show that she still had a full beverage and everyone’s eyes fell on it awkwardly. That had clearly been Anko’s only plan to get her away, and there weren’t many other options for a new one so-

**_SMASH._ **

You all looked down where the bottle now peppered the concrete in pieces, and liquid in a star-like pattern was strewn across the stones. 

“Whoopsie~” Anko chirped without a hint of actual remorse for having just slapped a drink from someone’s hand. “Please, let me make it up to you. Come on, I know the bartender inside _pretty well_ if you know what I mean. He’ll give you a new one for free!”

Before the poor girl could object, Anko had her by the shoulders and was pushing her away. Without the distraction of others, the air around Kakashi and you quickly grew thick and tense. Given that you were the ones to approach (which Kakashi was certain was not by accident), he wanted to give you the opportunity to speak first. But when you remained silent for more than a few uncomfortable, long seconds, he cleared his throat. 

“So-”

That was more than enough to get you started. 

“ _So,_ was she also trying to rescue a cat? Or were you planning on having her join us all along?”

It came out harsher than you meant it, but you weren’t planning on apologizing. Anko had given you specific instructions to take this opportunity she was giving you to ‘dominate the playing field’ and ‘let him know you knew what was going on’. Which was almost laughable, because you really hadn’t a clue. All you knew was that something -some _burning_ feeling- was curling in your gut at the thought of Kakashi replacing you so quickly, and you didn’t have an issue with expressing _that._

Beside you, Kakashi blinked. He understood that you were upset. Hell, he wasn’t too happy with the whole situation either; none of it had been his idea after all. Still, he hadn’t expected you to come on so strong and honestly he wasn’t sure he appreciated it. He certainly hadn’t planned on being malicious himself, but he also wasn’t above meeting you at your own level either. 

So he gave a casual shrug, eyes dark. “You said you had other plans.”

You let out a scoff. He was trying to get under your skin. As a school teacher, you knew what it felt like to have someone test your boundaries, and you knew you should have walked away. At the end of the day it had only been one drink, and Kakashi was one guy, and you didn’t need a guy in your life anyways. 

But a feeling of desire deep inside you made you want to see this through. 

“Well what a good thing I did. I’d hate to be an imposition on your little reunion,” you spat with venom on your tongue. 

Kakashi flashed you a sideways glance. “And yet here you are.”

Your mouth gaped. Honestly, the _audacity._ Placing your hands on your hips, your lips curled into a deep frown. “If you didn’t actually want to go out again, you could have just said so!”

Finally Kakashi turned to you, an amused glint in his single eye. “Hold on now,” he drawled, leaning in. Your heart skipped a beat as the space between you lessened. Kakashi stilled only inches from you, his presence suddenly dominating and assertive. His breath tickled your skin as he spoke and heat rose to your cheeks. “I believe I was the only one who said _I did_ want to go out again.”

You squirmed under his knowing gaze. At your core you believed you were in the wrong. Honestly, Kakashi asking out someone else after you rejected him wasn’t too different from you ditching your date the other night to go out with Kakashi instead; everyone had to shoot their shots. But, you were far too stubborn to admit that now and it would be a lie to say you didn’t recognize the twisting feeling in your gut as a little bit of _hurt._

So instead of backing down, you continued to kindle the fire. 

“Sorry,” you spit, turning from him “I must not have heard you over the shrill voice of your _new date._ ”

Kakashi remained relaxed. You swore you even saw a grin tugging at the corners of his mouth, as if he were amused by your combative responses. “If you’d like to take her place, all you have to do is say so.”

 _“I don’t.”_ You didn’t allow yourself even a second to think about it. 

You heard him let out a slow and warm chuckle. “Ah, are you sure?” Before you knew what was happening, your hand was being tugged into Kakashi’s gentle grip. He turned your wrist upward, and with his other hand he placed the pads of two soft fingers to the veins under your skin. His steady gaze locked with yours. “Your heart rate says you’re lying~”

Had any other man dared to call you out like that, you might have decked him. You weren’t usually one for making exceptions either, but the moment Kakashi’s fingers grazed your skin, you had to resist the urge to melt like putty into his touch. Something about it just felt right, and you craved it all over your body. The desirous glimmer you saw flash through his stare told you he craved you too. 

You wanted to speak, but every word was caught in your throat and your mouth was suddenly dry. 

“I-”

“Ugh, I don’t know what’s gotten into her! Kakashi, maybe we should move- _Oh._ ”

It takes a second for you both to pull your eyes from one another and turn to see the woman Anko had pulled away now back in front of you. Her pupils had narrowed and she was locked on to your upturned palm which was still being cradled gently in Kakashi’s own.

“Am I interrupting?” she stammered out hesitantly. There was also a hint of bitterness in her tone that you couldn’t miss. 

You tugged your hand away from Kakashi and clutched it to your chest. 

“No, I was just leaving actually,” you said softly, the contention between you and Kakashi now gone. “Sorry about Anko. You two enjoy your night.”

You said nothing else as you turned from the bar and headed inside to find your wingwoman. With your back turned, Kakashi couldn’t see the way you kept your hand close to your heart, encasing it with your other fingers in an attempt to replace the soft, comforting grip that you had just pulled it from.

**Notes for the Chapter:**

> And our poor lovebirds story continues~
> 
> Thank you all for reading, as always. I hope to see you in the next chapter as well! It's late here so I'm going to bed cuz ya girl is sleeepy.


	4. Round and Round

“It’s been a week,” Kakashi said, because it had. 

It had been exactly one week since he talked to you last. One week since he got to hold your hand, and let his fingers brush over yours in a way that -even if only for a moment- brought him such a sweet feeling of happiness that he hadn’t felt in a long time, or possibly ever. The things he felt around you were still such a distracting, _frustrating,_ mystery to him. When he pictured your pretty face in his mind, his heart fluttered. A few times he saw you in the market, only a few feet from him in the crowd, and he felt this sickening flip in his stomach. Like he wanted to say something, or maybe reach out and hold your hand again, if you’d let him. 

He was getting that same feeling now, after his eyes singled you out in the usual morning crowd of Konoha’s streets. From where he sat in the small cafe you couldn’t see him, but that didn’t make the lump in his throat any smaller. He took a sip of his drink, only to spill it on his mask with a disheartened grumble. 

When he thought about just moving on and abandoning the pursuit of any type of relationship with you, he felt a pang of guilt and -of all things- regret. Because more than anything, he felt a desire to spend just a little more time with you. It was nauseating, and completely involuntary. Invasive, really; why did any of it make him so excited? 

If you had asked him one week ago what could have cured such a horrible ailment, he would have guessed time, or maybe some fancy herbal tea that he couldn’t pronounce. But now it had been a week, and he wasn’t feeling any type of relief from his lovesick heart. And he had tried several teas, all of different varieties, and none of those helped either. 

The cup his fingers were currently wrapped around was probably his least favorite of the few he had tried so far, and it didn’t help that it was now soaking into the cloth covering his face. Kakashi wrinkled his nose and gave a deep sigh as he set it on the table and pushed it away from him. 

Across from him, Asuma gave a small snort. “Don’t tell me, you’re getting desperate already? You’re still just in the beginning stages of this; it’s supposed to be fun.” 

Kakashi’s brows raised in disbelief. “You honestly think this is _fun?_ ” he wheezed, genuinely not sure if he was the weird one for finding all of the butterflies rather uncomfortable. 

Asuma smiled and took a sip of his black coffee. “Well yeah, new relationships always are,” he said with a thoughtful look. “There’s something special about those first couple months when you’re still just getting to know each other, you know?” 

“Months?!” Kakashi sputtered in response. Asuma offered only a shrug in return, and Kakashi almost fell out of his chair. He couldn’t possibly be feeling this way for months, could he? His eyes spun at the thought of it, and he dropped his chin into his palm. “Well, it seems it would be a lot more fun if she was actually around. I haven’t had a chance to learn anything about her since we tried your strategy.”

There was an accusatory bite to Kakashi’s words, which Asuma brushed off with a wave of his hand. “Yeah well, don’t worry too much about that. She’s only giving you the cold shoulder because Anko told her to. I’m sure of that.” 

Underneath his mask, Kakashi frowned. He wasn’t so sure of it. He wasn’t sure at all that he hadn’t royally pissed you off and forever ruined his chances of getting to know you better, thus sticking him with these dreaded feelings for the _rest of his life._

Asuma, oblivious to Kakashi’s spiraling thoughts, continued casually, “She’ll come around soon enough. Once Anko tires herself out anyways.” He downed the rest of his drink and set the mug back on the cafe table with a little clink. 

Kakashi grumbled and rubbed the corner of his uncovered eye with his knuckle. “This is all starting to feel very trivial, don’t you think?” he stated more than asked. How long was he expected to wait exactly? Was waiting for you to come around really the right thing to do, anyways? Regardless, Kakashi didn’t think he would make it much longer. He wasn’t exactly sure what would happen if he went on this way either, but he was sure it couldn’t be anything good. Besides, as far as he could tell, there was only one solution to his problem and it currently stood about a hundred feet from him. Looking perfect and pleasant. 

His eyes sparkled with just a hint of excitement when he said, “Can’t I just go talk to her?”

Asuma glanced lazily over his shoulder, following Kakashi’s gaze to you. You were picking out a few things at the local bakery. You were casual and clearly unaware of your gawking onlookers. Sure you looked pretty-as-a-picture while minding your own business, but you were honestly just doing some necessary grocery shopping for the week. Nothing special really, but when Asuma looked back to his silver-haired friend and saw the entranced look in Kakashi’s eye, he realized just how special Kakashi thought you were, and the corners of his mouth curled a little. Asuma began to think it didn’t much matter what he said next. 

“You want my honest opinion?” the brunette asked despite knowing his friend’s mind was already made up. 

Kakashi wasn’t so sure yet, and so he thought it over for just a minute. Asuma had mentioned more than a few times that you were most likely ignoring him in hopes of getting some sort of desperate response from him, per Anko’s instructions. Maybe that was true, but he didn’t think he cared much about that anymore. He just wanted to talk to you again, like he had that first night he met you. 

Kakashi continued to watch your movements carefully. You handed a few coins to the man behind the counter of the shop and then turned to walk down the road. To walk further away from him. 

He stood from the table with an almost alarming jolt. “No,” he said to Asuma, finally answering the previously asked question. “I’m going to go talk to her.”

Asuma placed a cigarette between his lips and gave Kakashi a teasing little glance. “I think it’s a trap,” he said, lighting the stick.

Kakashi tossed his head and in a flat tone replied, “And I think I said I didn’t want your opinion.” 

Asuma chuckled, taking no offense to the comment. Stepping around the stools and tables in the cafe almost clumsily, Kakashi gave a final little wave to his friend before heading out into the street and towards you. 

///

Asuma was -in a roundabout way- correct to think that Anko had instructed you to keep up the cold shoulder in an attempt to get Kakashi to chase you, because she _had._ The conversation just hadn’t been as direct as one might have assumed, because your opinion of all of this (not that anyone had asked) was that it was childish and silly, and you already had about twenty childish and silly things to look after everyday, you didn’t need another one in your life. 

“This is ridiculous Anko,” you had said to your friend after the encounter with Kakashi and his new date at the bar last week. “I just want to drop it.” You shoved another bite of the takeout into your mouth; you had insisted Anko stop with you to grab it after such a disappointing night out. 

“Of course it feels ridiculous, we were going about this the entirely wrong way,” Anko explained, her own cheeks stuffed as she spoke. “Kakashi isn’t just _some guy_. If I had known he was who you were getting all goo-goo-eyed over, I would have told you to go on that second date.” 

A deep scowl painted your face. “You’re all over the place!” you spat, a chopstick almost flying from your grasp.

Anko clicked her tongue, “Misinformed, is what I think you mean.” 

You only rolled your eyes. It didn’t matter to you what you called it, you weren’t able to keep up with her or her plans and you were at the end of your wits already, but Anko didn’t seem to notice.

“Kakashi’s too smart for mind games. Not to mention he’s used to attention, and if you lay it on too thick, he’ll just drown you out,” she continued on between gulps of water and bites of food. “I’ve seen it. Whenever he comes to the bars with our usual group, the younger girls lose their mind over his pretty face, but I don’t think I’ve ever seen him give one of them a second glance.”

The corners of your lips turned upwards into a smile without you even realizing. 

“Look, Kakashi likes to have the upper-hand,” Anko puttered on. “So you’ve just gotta deflate his ego a little. You know, show him how cool you are.”

You blinked at the violet haired girl and -having just shoved another very large bite of your midnight snack into your mouth, causing your cheeks to fill up like a squirrel’s- an awkward silence quickly filled the air around you. You chewed a few times and a little bit of rice fell from your lips and into your lap as you said flatly, “But I’m not cool.”

Anko snorted, sending you a bit of a glare. “Well not with that attitude.”

You dropped your chopsticks and grabbed your water to help you wash down the last bit of the oversized bite you had taken. Honestly, this was becoming too complicated. You and Kakashi had gotten along just fine until your friends got involved. Why couldn’t you just try that again? Sure, it stung that he decided to go out with another woman (even if it was just to make you jealous), but perhaps that wasn’t so bad after you denied him in the first place. Wait, was this mess your fault for listening to Anko? 

You shook your head, just before it began to hurt from all of the overwhelming thoughts. “Ugh, I don’t even care anymore!” you spat, pushing your takeout container across the table from you. You weren’t sure you meant it, but you hoped that maybe you could speak it into truth. 

If there was any seriousness in your tone, Anko completely missed it. “Yes, that’s perfect!” she smiled, applauding your nonchalance. 

Flatly you responded, “No, I mean it.”

“There you go, you’re really selling it!” 

You huffed, but said nothing more. Really, you should have known by now that there was no stopping her once she made up her mind about something.

“If Kakashi realizes you still don’t care, even after Asuma’s little jealousy stunt, he’ll try to get your attention again soon. Trust me.” Leaning across the table with a cat-like grin she said, “And that’s when _you_ get the upper-hand!”

So while you carried on with your week and attempted to keep as much routine as you could and bury yourself in your work in order to forget the whole dating ordeal, Anko believed you were vehemently following her orders, and she was excitedly waiting for the day you would come back to her with more gossip to share. 

For the most part, it was working. You had plenty of things to keep yourself occupied, like your project for the academy, and shopping for the week, like you were doing today. Sure, there had been a few times when your mind had wandered back to the man with starlight hair that had so _boldly_ entered your life one week ago and _audaciously_ ignited feelings inside of you, but with a little time you were sure you could move on. 

With a kind smile, you paid the shop owner for the items in your basket and turned with a small wave. Yes, just a little time and a little normalcy in your routine would surely clear your mind of _Kakashi Hatake._

“Hello!”

You stopped short with a frown, the dirt beneath your feet sliding up into your sandals and in between your toes at the abruptness of it. 

The greeting was cheerful, innocent even, but still you were cursing whatever gods would hear you when you turned and saw the half-covered face of a silver-haired ninja. You couldn’t decide if this was some type of twisted destiny, or if Anko actually happened to be right again, but you didn’t give it too much thought before you spat back.

“What are you doing here, Kakashi?”

The ninja shifted on his heels when you strode past him, and casually fell into step beside you with his hands in his pockets. “Oh well, I was actually on my way home when a mysterious man emerged from the woods -I prefer to take the scenic route, you see- and he warned me that if I didn’t buy fresh milk for my cat she would fall ill-”

You looked at him sideways, the skin over your nose pinching together in annoyance. “Do you even own a cat?”

Kakashi stopped. “Huh, that’s funny...” He tilted his head, his eyes widening in realization. “You know what, I don’t think I do. Guess I don’t need to buy milk then!”

You grumbled, using all of the air in your chest to suppress a giggle. “You’re unbelievable,” you spat, your pace quickening just a little. 

Kakashi gave a casual shrug and continued, keeping up with your stride easily. “Well anyways, I’ve been thinking that maybe things got a little out of hand the other night-”

“I don't know what you’re talking about,” you said, almost too quickly. 

“No?” Kakashi asked, a teasing tone in his voice. “So it’s just me who remembers how wildly your heart was beating? Am I making that up? My mistake-”

You let out a little groan and accidentally bit your lip as you did. You brought your hand to your cheek and grimaced, “What do you want, Kakashi?” Your tongue massaged the soft, swelling skin on the inside of your mouth, and you almost bit the tender spot again when Kakashi stepped in front of you, his broad shoulders and deep stare practically caging you in under their penetrating gaze.

“I just want to get to know you,” he remarked, like it was the most innocent thing in the world. For a second, your heart stilled and as you peered up at him, you wondered if it really was just a harmless request. 

“I think the real question here,” Kakashi continued, “is what do _you_ want?”

You stood beneath him, holding your hand to your cheek though you hardly noticed the pain anymore. What _did_ you want? You liked him, didn’t you? Yes, way more than you cared to admit and that was the problem. You didn’t want to date. You hadn’t wanted to be out on that date a week ago, and if you had known that asking Kakashi out for a drink would have led to a silly little crush, you would have skipped the whole thing, because you did not _need_ a man in your life. 

As easy as that was to say, it didn’t stop the fluttering of your heart when Kakashi leaned just a little closer, waiting eagerly for your response. 

“I-” you started, unable to string any words together when Kakashi stepped even nearer with a curious little hum. "I don't need anything-" you finally retorted, puffing your chest out just a little and feeling confident, but Kakashi then cut you off almost immediately.

"Ah-ah, that's not what I asked," he tutted playfully and you felt as if you were beginning to shrink when he repeated, "What do you _want_ , Y/n?"

Your breath stuttered. Your heart raced. Your fingers twitched around your cheek, desperately aching to reach outwards and brush themselves along the lines of Kakashi's mask. You wanted to touch him again, you wanted to give in to his silly little attempts to woo you, you wanted to let him get to know you, _but_ -

“I want you to convince me.”

_But you were so scared._

Your fingers dropped from your cheek and into a fist at your side when you finally stepped away and strutted around Kakashi. Though they came from your mouth, the words hardly felt like your own.

Kakashi hesitated and fell a few feet behind you. “Convince you?” he blinked. 

“Yes.” You said, the words coming out in a frown. “If you really want to get to know me, then prove to me that you’re serious. Show me you’re worth more of my time, and not just some stupid mistake I’ll regret in a few months.”

Perhaps it was a little demanding, but you knew your value. You weren’t going to open up to someone who was going to bail when you asked them to put in a little work. While others passing by might have thought you sounded harsh, or maybe even startling, Kakashi wasn’t deterred. 

After regaining some composure, he called back out to you, “Alright then, and how do you suggest I do that?”

“I don’t know,” you responded with a lazy shrug. “You’re smart. You figure it out. But,” -you glanced over your shoulder, a sly little smile finally forming in your gaze- “maybe don’t ask Asuma for any advice this time.”

///

“ _Kakashi Sensei!_ Ugh, where is he?!”

The man in question poked at a few stray leaves stuck on the roof he had been resting on, and continued to ignore the shouts of his irritated students below. He still had a little bit of time before he was _unusually_ late. 

“Sounds like a lot of work to me,” Kakashi’s four-footed companion said in response to hearing about the jonin’s current predicament. He gave a bored sigh and licked a paw that he then used to rub his face clean. Pakkun didn’t care much for gossip, but he couldn’t help but be a little curious that his own master was taking a special interest in someone. “Is she really worth it?” the small dog asked, with a hint of genuine concern framed in the question.

“I think so,” Kakashi responded after a long moment of thought. “It’s odd though. I can’t really explain why I feel that way…”

Pakkun paused. He wasn’t sure he was really the best at giving advice, and if he were being honest, he was a little surprised when Kakashi had summoned him to talk about a _girl_ of all things. But from the sound of it, this wasn’t just any girl either. Maybe he could find a way to help. 

With a little woof he asked, “Well, what do you know about her? What does she like?”

Kakashi’s eyes widened, suddenly looking void of any thought. “What does... she like?” he stuttered, admittedly a little stupidly. Pakkun only nodded and Kakashi took a moment to think. You two had talked for a long time on your first outing together, but you hadn’t really gotten to likes or dislikes yet. He tried to think back to anything that might be helpful. “Uh, she’s passionate about her work at the academy,” he said in a voice that wasn’t at all confident. 

Pakkun nodded. “So she likes kids then? One of those maternal types maybe?”

“I suppose so…” Kakashi could only assume that was true because he didn’t really have anything else to use at this point. 

Pakkun began pacing at his feet. “Alright, let’s work with that then,” he said.

Kakashi let out a defeated sounding sigh. “How? I don’t have any kids-”

 _“KAKASHI SENSEI!”_

The shout from below was even louder this time, and caused both Pakkun and Kakashi to startle. 

“Where are you, you lazy ninja!? You owe us two hours of our lives back!”

After Naruto quieted, Pakkun's tired eyes drifted back to Kakashi, who was beginning to show a little look of realization. 

Pakkun gave a little chuckle and responded, “Are you _sure_ about that?”

**Notes for the Chapter:**

> Ooh hey pals, it's been a minute huh? All the same, I hope you enjoyed this little addition. I am very excited for the next chapter, and will probably end up laughing the whole way through it, but that hopefully shouldn't cause any delays. It shouldn't take nearly as long to get out, but y'know fam, it's 2020. We're all just rolling with the punches at this point. The trash can in my bedroom is literally just full of sour patch kids wrappers from halloween.
> 
> Thanks for sticking with me though! I appreciate you all. Until next time you can bug me on [tumblr](https://aerinth.tumblr.com/)


	5. If First You Don't Succeed

Team seven hadn’t been together very long, but already they had grown accustomed to the extreme tardiness of their silver-haired sensei. It had become the norm to wait on him, for sometimes hours, but by no means did that ever make the final arrival of their teacher any sweeter.

“Good morning!”

Naruto whirled around with an accusatory finger already pointed in the direction of his masked teacher and a look of pure aggravation plastered on his face. “There you are! What the hell Kakashi Sensei, what took you so long?! Never mind, I don’t want to hear any of your _lame_ excuses. When are you finally going to teach us something cool!?”

Kakashi frowned, deflated. That was the reaction he received after being so polite? How rude. Also, he didn’t think his excuses were _lame._ He worked really hard on them most days.

“Oh come on guys,” Kakashi hummed, trying to soften the tension of his team. Though Naruto was the one shouting, Sakura and Sasuke didn’t look any happier to see him. “You know what they say: anticipation makes the heart grow fonder!”

This time Sakura snapped too. “That’s not what the phrase is!” she and Nartuo chided in unison.

“Anyways,” Kakashi gave a wave of his hand. “I’ve got something special planned for the lesson today, and it is pretty cool. At least I think so.”

His irritation doing a complete one-eighty, Naruto’s eyes began to sparkle with excitement and he started listing all of the things he hoped his wise teacher would be instructing them on: a powerful jutsu, how to use a new type of weapon, _how to fly._ The boy’s imagination raved on. Though he kept to himself about it, Kakashi noticed that even Sasuke’s interest seemed to have peaked at the mention of a ‘special’ lesson plan.

“Today’s lesson,” Kakashi interrupted Naruto’s squawking, “will be on the _art of espionage._ ”

Naruto pursed his lips and blinked owlishly. “Uuuuh, espionage? What’s that?”

Sakura didn’t suppress her groan of irritation. “Naruto you idiot, didn’t you ever pay attention in class? Espionage is when you gather information from your enemies without them noticing. It’s a huge part of missions, and how much or how well you gather the information could completely determine the success of your team!”

Kakashi nodded. “Exactly, Sakura. Very good.”

The young girl smiled brightly, eyeing her more stoic team member and Naruto rolled his eyes.

“Sounds like a lot of work to me,” he grumbled, already growing less excited for the activity.

All the same, Kakashi carried on explaining the task he had planned for them. “Today you’ll get hands-on practice gathering information discreetly. Your only instructions are to gather specific information from the target. There are no rules to how you go about gathering the information, but If you get caught by the target, or don’t gather any useful information, then you fail. So, use what you’ve learned in your training so far to help you through the exercise.”

“Who’s the target?” Sauske asked, serious and straight to the point as always.

Kakashi gave him a casual sideways glance. “I’ll get to that in a moment.”

Naruto, still sounding skeptical, asked, “Well, what kind of information do we have to gather?”

“Nothing too complicated,” Kakashi shrugged. “Just a few basic details about her interests. For example, things she likes or dislike. Or maybe some things that would impress her.”

Naruto and Sakura eyed Kakashi suspiciously.

“So you want us to find out what some _girl_ likes?” Naruto clarified.

The jonin stayed firm in the instructions he had given. “That’s right,” he nodded.

Sakura touched her hand to her chin and thought for a moment about why exactly her teacher might be asking them to spy on a girl, before she let out a little gasp of realization. “Hey, wait a minute. Does this have anything to do with Y/n Sensei?” Sakura questioned, her brows falling into an accusatory glare.

“What?” Kakashi stammered, genuinely surprised that his student had drawn the conclusion so quickly. “What makes you say that?”

Sakura frowned, her irritation growing after seeing Kakashi react so honestly. “Because I saw you two out in the market yesterday, and she totally _snubbed you!_ ”

Coming to the realization that Sakura was right about this, Naruto groaned. “Ah, are you kidding me?! You’re trying to use us to get a _girlfriend?_ Ugggh, gross!”

“I can’t believe you tried to trick us!”

Even Sasuke let out a little scoff.

“Hang on a minute guys-” Kakashi tried to explain, but Naruto hollered again.

“Jeez, I thought you said this would be cool! Don’t make us suffer with extra work just because Y/n Sensei doesn’t like you and probably thinks your hair is goofy!”

A little whimper of dejection escaped Kakashi. First lame and now _goofy._ This wasn’t going as smoothly as Kakashi had hoped. He had been called out by one twelve year-old, and insulted by another before the exercise even started. They really weren’t holding back today.

“Alright, alright,” Kakashi finally interrupted taking control of the conversation again, albeit with a little less pride than he had before. “Regardless of the intention here, gathering information discreetly is still an important skill for you all to practice,” he said with a little sigh of defeat. “But, since you all don’t seem to be so easily convinced, how about we make this a little more interesting?”

Once again he had his students' attention.

“Anyone who doesn’t fail will be treated to dinner by me,” -Kakashi paused, and the three leaned in- “For a _week._ ”

He had hoped he wouldn’t have to resort to such frivolous incentivizing, but it was the only back-up option he had come up with in such a short time, and clearly it was working because Naruto immediately erupted in frantic delight.

“Oh man, that’s what I’m talking about! Free ramen for a whole week? You’re on, Kakashi Sensei!”

Beside him, Sakura bit her lip in an attempt to contain her excitement. What she said was, “Oh wow, that would be great Sensei.” Though what she was thinking was, _“Sweet! I’ve been dying to try that new Kaiseki restaurant, but it’s so expensive!”_

Kakashi immediately got the feeling that he might come to regret this bribery later. Still, he shifted a lazy gaze over to the third member of the team who hadn’t chimed in yet.

“Sasuke?” Kakashi encouraged, and Sakura and Naruto looked at him with anticipation.

After a moment, the boy gave a little shrug. “Whatever,” he huffed, though the slight glimmer of hope in his eye wasn’t missed by his teacher.

“Perfect,” Kakashi smiled, now that everyone was finally on the same page. “So, who wants to go first?”

///

It was later in the morning than usual when you finally left your apartment and began your almost daily walk to Konoha’s academy building. There were significantly more people out on the street than you were used to, and the path was a little muddy from some rain the night before, but otherwise nothing had felt out of the ordinary on your trip- until you turned a corner off of the main road. Fewer people lined the path now, and you suddenly felt a chill of vulnerability rush up your spine.

A feeling like you were being _watched._

You hesitated for a minute, taking a breath and assessing your surroundings to determine if you were actually being followed or if maybe you were just being a little paranoid. After a comfortable amount of time had passed, and nothing else happened, the hairs on the back of your neck finally flattened and you carried on your way to the school.

It wasn’t until you rounded the fence line of the courtyard -where you could hear a few kids playing tag- that you once again experienced that same creeping feeling that some type of threat was nearby, watching you. You couldn’t imagine why anyone would be trailing you, but you were certain someone was close and you would give up your own life before you let any danger near your students.

When you halted on the path again, you felt the sneaking presence behind you stop as well, and you knew it was no mistake. You took one single grounding breath, and then spun around on your heel hoping to catch the person off-guard, but prepared to counter if they decided to attack.

Much to your surprise, no one scurried, or lunged, or even moved at all. There was no one there. No one at all. You relaxed, and just as you began mumbling about being paranoid and out of practice, you caught the briefest glimpse of dark eyes poking out from around the corner of the fence line.

Your gaze narrowed and you stepped forward. “Huh? Sasuke is that you?” you asked, immediately recognizing the raven hair and serious eyes of your former student. He had graduated since you left for your trip, so it had been two years since you had him in your classroom, but as a good teacher you never forgot your students.

Around the corner, Sasauke brought a hand to his forehead and gave an irritated grumble. He had been so confident that he was being careful, but he realized now he had underestimated your wit and intuition. A terrible mistake to make on any real mission.

Recognizing that he had been caught, Sasuke stepped out from around the fence looking rather irritated and even a little embarrassed. His gaze fell to the ground and he crossed his arms, seeming to be thinking hard about something.

You took another cautious step towards him. “It’s been awhile since I’ve seen you. Is everything okay?” you asked, noticing his uncomfortable body language and the way his jaw clenched when his eyes shifted back to you.

“Yeah,” he finally said in a voice that was so uncomfortable you didn’t believe him. “I just-” he tried, but he stumbled. It was only getting harder for him to find the words when you stepped closer yet again.

“Listen Sasuke, if you’re in some kind of trouble, you can tell me,” you offered gently, reading his discomfort as a sort of cry for help.

Sasuke grimaced. His plan for this little mission was falling apart at the seams. Your eyes were so wide and curious, it was honestly intimidating how much you looked like you cared. You bent over just enough to be at eye level with him, and he began to feel suffocated with your big, sincere, e/c orbs pressuring him to say something. _Anything._

“I need your help with something,” Sasuke finally spit up, trying to think quickly on his feet. Maybe if he could tap into your more nurturing side, he could still find a way to gather the information Kakashi wanted without completely outing his teacher. For the most part it was a good plan except...

Except that asking for help was so _terribly_ foreign to the Uchiha boy, that when the request fell from his lips it sounded frightened and desperate. He had definitely tapped into your more nurturing side because you let out a little gasp and took his hand in yours, much to Sasuke’s surprise. It was out of complete instinct that you squeezed his soft palm reassuringly and spat out the first thing that came to mind- since it was usually what followed when your students told you they needed help in such a fearful tone.

“Sasuke, are you being _bullied?_ ”

The boy went rigid.

Coughing out some sort of denial, he immediately tore his hand from your grasp and turned away, his face turning an even rosier shade of pink by the second. Before you could ask any further questions, he managed to spit out a coherent, “Forget it,” before disappearing completely.

Alone again, you blinked. You knew Sasuke had always been a little troubled, but that was unusually odd in your opinion, and honestly you were just utterly confused by the entire interaction. You decided that the least you could was check in with his team leader about it. Though, you quickly realized you didn’t actually know which teams most of your students had been placed into, and so you made a mental note to look those up later.

But for the time being you would dismiss the strange interaction since there was nothing else you could do about it now. Turning back around, you headed into the building for your day of work. Down in the courtyard, you couldn’t hear Nartuo up on the roof wheezing with laughter at Sasuke’s terrible display of discretion, or see the look of uncertainty on Kakashi’s face when he realized that his only hope now was Sakura and Naruto.

///

Despite running late to work that morning and having a very unusual engagement with your former student, your day of work went smoothly, and you felt motivated and excited to begin your over-time working on the restructure project. You had been working for a good hour or so before you heard the door to your room slide open, and saw the young doe-eyed kunoichi enter your room with a little wave.

“Oh hi Y/n Sensei! How funny running into you here,” Sakura smiled, following up with a forced laugh.

You raised a brow at the girl. You probably wouldn’t have found this to be too unusual if you hadn’t already had one strange encounter with a previous student. Maybe she was just lost but, “Um, Sakura this is my office?”

“Right! It is. Silly me,” she laughed awkwardly, though she came to sit in a vacant chair across from your desk anyways. “I just forgot because you were away for so long. Speaking of, how was your trip Sensei?” she smiled brightly. Innocently, almost.

Something was off, you were sure. But since you couldn’t quite put your finger on what yet, you responded simply.

“It was a lot of hard work, but I learned a lot and that’s what matters,” you said, thinking back on your experience fondly.

Across from you, Sakura nodded. “Totally! Still, you got to go to so many places, you must have met a lot of people?”

She eyed you expectantly, to the point that it was almost uncomfortable.

“Uh, yeah, I suppose so-”

“Anyone special?” she cooed, cutting you off.

You stared back at her for a long moment. There was something you were missing for sure, but you were honestly thrown off guard by her directness that you were struggling to navigate your way back. “Sakura,” you started, a little cautiously, “was there something you needed from me? If not I should probably get back to work.”

She had clearly not been expecting you to be so direct in return, and almost immediately you felt the desperation in her rise.

“Actually-!” she spat out, sounding so frantic it made you jump a little. Unable to finish her thought, she took a deep breath and let her body release the tension of her facade.

“Yeah, actually there is,” she admitted, much more softly this time. “Sorry for acting so weird, Sensei. I should just be honest and ask you. What I want to say is hard to put into words, and I don’t have many older women role models in my life that I can talk to about this stuff, you know?”

Your brow twitched a little. _Old._ She had said _old._

“Well, I’m happy to help in any way I can.” You smiled as sweetly as you could for an _older woman._

Thankfully Sakura didn’t seem to notice your discomfort, since her gaze had fallen into her lap where her hands sat folded, thumbs dancing over one another nervously. “Well,” she started, “How do you know if a guy is the right one for you? Like, what are things a woman should look for in a good man?” Her eyes flickered up to you, a little shyly. “What do _you_ look for, Y/n Sensei?”

You pondered her question for a long moment, tapping your pen against the open book on your desk. Now that you thought about it, it wasn’t that odd for Sakura to be asking about boys at her age. Still you couldn’t help but feel a little odd dishing out relationship advice to such a young girl who had plenty of other things ahead in her future besides boys.

You dropped your pen down and looked at your student with a soft gaze. “I think it’s less about looking and more about letting the relationship happen naturally, does that make sense?”

Sakura only blinked, so you tried to explain further.

“See, I’ve always heard that when you do finally find the right person, you’ll just _know_ somewhere in your heart. But honestly Sakura, you don’t have to have a boyfriend to be happy.”

Sakura fidgeted in her chair and bit her lip. “I know that,” she said in a voice so small that made it sound like she was trying to convince herself. “But don’t you think it would be nice to have someone special? You know, just to go shopping or out to dinner with sometimes?”

You gave a little shrug, and nodded in cautious agreement. “I suppose,” you said, “But you can do those things yourself. You don’t have to wait for a man to take you to dinner _to go to dinner_. What are you going to do if the perfect man doesn’t show up? Never go out to dinner, or go with someone you don’t like?”

Sakura stilled. Her expression became puzzled. “Huh... I guess I never thought about it like that.”

As she continued to think about this perspective you asked, “What’s something you’ve always wanted a boy to do for you?”

The question immediately brought a dusty pink blush to Sakura’s pale cheeks. “Oh well, I’ve always thought it was really cute when a man buys his girlfriend flowers!” she giggled. “Not for any reason really, except to say that he really likes her!”

Her romantic spirit was endearing, you had to admit. But if she wanted your honest advice, you were going to give it. “That is cute,” you agreed, but added, “Why wait for a boy though? You like yourself, don’t you? Go buy yourself flowers!”

Sakura’s mouth fell open at the thought, and you gave her a confident reassuring smile. “One day I hope someone special buys you flowers for no reason, Sakura. But until that happens, you can buy them for yourself.”

For a moment, she seemed completely startled at this thought. But as the idea floated around her mind and the more independent part of her personality was awakened, her face began to brighten with a smile of total confidence.

“Yeah!” she exclaimed, jumping to her feet. “You’re right, Y/n Sensei! I don’t need a _boy_ to buy me anything, I can do it myself!” She thanked you, and with a newly found pep in her step, she skipped straight to the door.

“Oh! Okay, you’re welcome!” you called after her with a wave. “See you later.”

With this realization that there were so many things she wanted to do for herself, Sakura felt like she was walking on air as she headed down the hallway from your office. It wasn’t until she basically collided with her squad leader -who had been waiting, and _listening_ \- that she realized she had completely and totally lost track of the whole conversation. Instantly, she wilted with a sigh.

“Oh man,” she moped, hanging her head. “I failed, didn’t I?”

Kakashi only nodded with a frown. “Yup.”

///

Two of his students had already flopped and now -Kakashi sighed- it was up to Naruto. The most rambunctious and overpowered of his three children. He was worried about the blonde feeling apprehensive after watching Sasuke and Sakura’s inadequacy so he had asked Naruto what his strategy was, to which Naruto happily responded, “You just leave it to me, Sensei!”

Now perched on the corner of a rooftop, Kakashi had no choice but to watch -and judge harshly- as Naruto began his task in the streets of Konoha below.

Any confidence Kakashi was clinging to before, was instantly lost when Naruto sprang towards you in the road, completely cutting you off in your path, and said, “Hey, Y/n Sensei! I’ve got a little proposition for you!”

Startled, you just about dropped the groceries you were carrying into the mud. “Oh, Naruto,” you finally breathed, collecting your lopsided bags. “Hi.”

Naruto wasted no time in getting to his point, nor did he move to help you or let you continue walking home. “Listen, I’m supposed to ask you a few questions, but I know you’re a busy lady so I’ll cut right to the chase. You answer my questions, and I get someone to buy you dinner _three times_ next week! How does that sound?”

Above and out of sight, Kakashi smacked a palm to his forehead. Splitting the bribe maybe wasn’t the worst idea, but Kakashi certainly didn’t like the direction this was headed.

Below him, you finally managed to articulate a little, “Excuse me?” You were just on your way home for the evening with the vegetables you had picked up for dinner, what exactly was he even talking about?

Naruto leaned back and crossed his arms behind his head with a laugh. “I know right, it’s a pretty sweet deal. Okay so tell me, what kind of things do you like in a guy? You know, like, someone you would date?”

Your eyes widened as you stared down at the boy. “What? You too?!” you sputtered, getting the sudden feeling of deja vu. “Naruto, what are you going on about? Why are you supposed to ask me this?”

“Hey, that’s not part of the deal! I’m supposed to be asking the questions!” he scolded, and you couldn’t help but recoil a little at his blatant impoliteness. “So what, is it their eyes? Big muscles maybe? Body hair? What? I don’t know what girls like, what is it?”

He continued to list other things he could think you might be attracted to and your head began to spin so quickly with confusion and annoyance, you felt like it was going to explode. Finally, with a little stamp of your foot to shut him up you asserted, “Naruto, I am not talking about this with you!”

The young boy groaned, “Aw, come on!”

“No!” you stomped again, and this time he sunk down a little with a pout and stepped out of your way. With your chest puffed up, you gave him a curt little nod to say goodnight, and then moved around him.

Just as you passed, you heard Naruto mumble under his breath, “Yeesh, why couldn’t Kakashi Sensei have fallen for someone less _crabby_ …”

Immediately, you froze. Above you, Kakashi choked on the air he was breathing.

It took less than a second for you to start putting the pieces together in your head, and -watching the gears turn in your brain as you figured it all out- Kakashi absolutely debated if he should say his prayers and run now, because Naruto would _probably_ be fine.

“Naruto,” you hissed as you turned back around to face your former student. “Were you assigned to Kakashi’s genin squad after you graduated?”

Naruto, still pouting, didn’t seem to notice the shift in your tone at all or the flame of displeasure that sparkled in your darkening orbs when you looked down at him.

“Yeah, why?” he shrugged, and it was only by some miracle that Kakashi’s soul didn’t leave his body that very moment.

Was this parenting, he wondered? Watching all of your hopes and dreams be dragged down into a deep grave by the very youth you had nurtured, protected and trained to survive in this cruel, cruel world? How poetic.

“And Sauske and Sakura, they’re on your team too?” you clarified, though you were pretty sure you already knew. Sasuke was never as disorganized as he was this morning, and though it hadn’t seemed totally out of the blue, there really was no reason for Sakura to come to _you_ for romantic advice.

In front of you, Naruto shrugged. “Yeah, and what about it?” he asked again, though it was only a moment later that he remembered what the goal of his mission was and said, “Hey wait, I said I’m supposed to be asking the questions! Do we have a deal or what?!”

With a deep frown and a little exhale of exhaustion you turned your back to the young boy again. “Go home Naruto.”

“So you’re not going to tell me-”

“Now!”

Ultimately accepting his defeat, Naruto slumped and shuffled away with another little pout. In the quiet, you were finally able to organize your thoughts.

Kakashi had taken your little invitation seriously, even more so than you had expected honestly, and as you stood there you realized- there wasn’t a _single_ part of you that was mad about it. How could you be? Your biggest fear was opening up to someone who wasn’t going to work with you, and Kakashi had just sent in an entire team (of children to be fair, but it’s what he had) to try and learn more about you.

You couldn’t stop the small smile that tugged at the corners of your mouth.

Now that you had found the missing link to all of the weird encounters in your day, you were sure Kakashi wasn’t far away.

“Kakashi, I’m flattered,” you purred in a teasing tone. Biting your lip into a little smirk, you lifted your gaze upwards. Sure enough, the silver-haired man was now standing in front of you on the path with a guilty expression covered mostly by the mask over the lower half of his face.

“Introducing me to the kids so early? That’s risky,” you joked, earning a small smile from the jonin.

He rubbed the back of his neck sheepishly. “They are a bit of a handful,” he said, mostly apologetically. Still, you giggled in response, and he was pleased to know that you didn’t seem to mind their terrible attempts to interrogate you _too_ much.

“They’re cute,” you grinned. It had been nice to get to see your previous students all grown up, even if it was in rather odd conversation. “Not very subtle though,” you added.

“It’s a work in progress,” Kakashi sighed with a bit of a tired look. After a moment, his gaze fell back to you and there was an optimistic glimmer in his eye. “So then," he started cautiously, "Does this mean I’ve convinced you? Have you decided that I’m worth more of your time? Or am I still possibly just something you’ll regret in a few months?”

His tone was playful and not at all pressuring, but you still felt a little squeeze of uncertainty in the center of your chest.

You bit the inside of your cheek. “Maybe,” you said honestly. It was a sweet attempt, but you could feel your emotional walls standing firm and you knew you’d have to at least sleep on the thought. Were you _really_ ready to give dating - _real_ dating, with a _real_ person- a chance? You didn’t know, and so instead of a direct answer you stepped forward, placed a gentle hand on the front of Kakashi’s jacket and said, “You’re certainly getting warmer.”

Your gaze danced upwards, locking with his, and Kakashi stilled. The feeling of your hand on his chest, that look of hopeful trust that you gave him- it’s what he had been craving all week. Immediately it caused that flipping feeling in his stomach and the rapid fluttering of his heart. It started all of the ailments he had so desperately been seeking a cure for, only this time, he didn’t want them to stop. He heard Pakkun's voice in his head asking once again, 'Is she really worth it?' He still couldn’t explain why, but when you finally moved away leaving a cold spot on his chest, he knew the answer was yes.

Giving one final little glance in his direction you cooed, “Goodnight, Kakashi," and winked.

As you drifted out of the lights of the shops and into the night -your hips swaying in a playful way that he couldn’t help but notice- Kakashi completely agreed that all over his body, he did feel much warmer.

///

“Well, you all failed,” Kakashi remarked bluntly when he and his team were back together again the next day. “But I don’t really know what I expected, honestly.”

It wasn’t as if Kakashi had really anticipated any of the three would achieve perfection (he wouldn’t have bet his wallet if that was the case), but he wasn’t expecting them to do so poorly either. He was feeling less concerned about his own situation after seeing you the night before, but it didn’t at all make him feel better about his students' terrible performance. He _certainly_ wasn’t thinking one of them would be so careless as to blow his cover entirely.

“Naruto,” Kakashi scolded, turning to the boy mostly at fault for that. “You completely disregarded the purpose of this exercise.” Naruto was sitting on the ground with his knees pulled into his chest and an angry pout on his lips. “If you’re going to make a direct approach like that, it better be good. _That_ was terrible.”

Naruto only groaned in response, and Kakashi turned to the one female member of his young team. Honestly, she was the only one who had come remotely close to gathering information, but ultimately she still failed. “Sakura, she completely dominated that conversation and manipulated the direction of your questions. If this were a real mission, that situation could have been a lot more dangerous.”

Sakura sighed, moaning a little “Yeah, I know,” in return.

Finally, Kakashi turned to the last member of his team. “And Sasuke,” he started, “What _was_ that, exactly?”

Sasuke clicked his tongue and turned away.

“I guess that just means you’ll all have to train extra hard today,” Kakashi concluded, and the three genin weren’t happy about it. Even Sasuke’s terrible performance review wasn’t enough to give Naruto comfort now. The boy stretched out with an irritated growl.

“Man, I don’t get why you’re hounding us so much when we haven’t seen her in two years!” he argued. “If you want to know so much about her, why don’t you ask Iruka Sensei?”

Kakashi frowned and crossed his arms over his chest. “That’s entirely beside the point Naruto. This was still a test of strategy and you all blew it,” he said firmly with a nod. Though after he made his point, he straightened and added, “But tell me, why should I ask Iruka?” He did still have to figure out _something_ to do to woo you.

Naruto rolled his eyes. “Uuuh maybe because they hang out together like every single day working on some _boring_ project? Duh.” He said it like it was the most obvious answer the world, and he stuck his tongue out just to make extra sure that Kakashi knew he thought he was being stupid. “I haven’t seen him in days because he’s always so busy,” Naruto added as a mopey afterthought.

Kakashi sat with this new information for a long moment, before a tiny little flame of an idea sparked inside the back of his head. Honestly he did feel stupid for not thinking of it before. It was so obvious.

Kakashi was definitely still learning how to do this whole getting-a-girl-to-talk-to-him thing, but finally it seemed he was at least (maybe) headed in the right direction. And this time, he had a strategy all his own.

**Notes for the Chapter:**

> Welcome to the filler episode of Just Date Me, thanks for not skipping it because I promise there is a reason for the chaos, at least in my head!
> 
> I love you all very much. As always, thank you for the continued support, I have such a blast sharing these chapters with you. It makes writing so much fun!


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